2-[(E)-2-(Nitro-methyl-idene)imidazolidin-1-yl]ethanol.

In the title compound, C(6)H(11)N(3)O(3), the imidazolidine NH group is involved in a three-center N-H⋯O hydrogen bond, with intra-molecular and inter-molecular branches, to the nitro group O atoms. The centrosymmetric dimers that are formed are further connected by O-H⋯O hydrogen bonds between the hy-droxy and nitro groups into a two-dimensional polymeric structure extending parallel to (101).

Related literature

For related structures, see: Tian et al. (2010 ▶); Li et al. (2010 ▶). For background to neonicotinoid insecticides, see: Ohno et al. (2009 ▶); Jeschke & Nauen (2008 ▶).

Experimental

Crystal data

C6H11N3O3

M = 173.18

Monoclinic,

a = 6.9422 (2) Å

b = 8.7142 (3) Å

c = 12.9698 (4) Å

β = 94.153 (3)°

V = 782.55 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.31 × 0.29 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.967, T max = 1.0

4832 measured reflections

1539 independent reflections

1186 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.11

1539 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039280/gk2305sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039280/gk2305Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H11N3O3	F(000) = 368
Mr = 173.18	Dx = 1.478 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 2585 reflections
a = 6.9422 (2) Å	θ = 3.2–28.8°
b = 8.7142 (3) Å	µ = 0.12 mm−1
c = 12.9698 (4) Å	T = 293 K
β = 94.153 (3)°	Prism, colourless
V = 782.55 (4) Å3	0.31 × 0.29 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	1539 independent reflections
Radiation source: fine-focus sealed tube	1186 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 16.0355 pixels mm-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.967, Tmax = 1.0	l = −15→15
4832 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.045P] where P = (Fo2 + 2Fc2)/3
1539 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.7352 (2)	0.66673 (18)	0.73309 (13)	0.0428 (4)
H1A	0.7010	0.7696	0.7099	0.051*
H1B	0.8709	0.6509	0.7230	0.051*
C2	0.70406 (19)	0.65267 (18)	0.84644 (12)	0.0387 (4)
H2A	0.7338	0.5485	0.8687	0.046*
H2B	0.7932	0.7207	0.8851	0.046*
C3	0.4516 (2)	0.84632 (17)	0.89333 (14)	0.0481 (4)
H3A	0.4536	0.9106	0.8324	0.058*
H3B	0.5364	0.8904	0.9483	0.058*
C4	0.2490 (3)	0.82924 (18)	0.92650 (15)	0.0519 (5)
H4A	0.1570	0.8840	0.8802	0.062*
H4B	0.2396	0.8668	0.9964	0.062*
C5	0.36609 (19)	0.59107 (16)	0.88760 (10)	0.0296 (3)
C6	0.3790 (2)	0.43186 (17)	0.87112 (11)	0.0358 (4)
H6	0.4933	0.3920	0.8490	0.043*
N1	0.50847 (16)	0.68944 (13)	0.87087 (9)	0.0336 (3)
N2	0.21646 (17)	0.66554 (14)	0.92072 (10)	0.0403 (3)
H2	0.1119	0.6216	0.9370	0.048*
N3	0.23318 (18)	0.33545 (14)	0.88605 (10)	0.0371 (3)
O1	0.62388 (16)	0.55935 (12)	0.67291 (8)	0.0481 (3)
H1	0.5161	0.5949	0.6580	0.072*
O2	0.07390 (15)	0.38210 (13)	0.91700 (9)	0.0480 (3)
O3	0.25342 (18)	0.19348 (13)	0.86750 (10)	0.0580 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0326 (8)	0.0405 (9)	0.0571 (10)	−0.0014 (6)	0.0154 (7)	0.0017 (7)
C2	0.0258 (7)	0.0403 (9)	0.0499 (9)	−0.0013 (6)	0.0021 (6)	−0.0009 (7)
C3	0.0482 (10)	0.0322 (9)	0.0651 (11)	−0.0019 (7)	0.0120 (8)	−0.0064 (7)
C4	0.0552 (11)	0.0338 (9)	0.0689 (12)	0.0060 (7)	0.0210 (9)	−0.0038 (7)
C5	0.0292 (7)	0.0324 (8)	0.0274 (7)	0.0016 (6)	0.0026 (5)	0.0012 (5)
C6	0.0303 (8)	0.0324 (8)	0.0454 (8)	0.0010 (6)	0.0077 (6)	−0.0015 (6)
N1	0.0319 (6)	0.0298 (7)	0.0399 (7)	−0.0019 (5)	0.0087 (5)	−0.0032 (5)
N2	0.0329 (7)	0.0329 (7)	0.0568 (8)	0.0031 (5)	0.0162 (6)	−0.0007 (5)
N3	0.0389 (7)	0.0323 (7)	0.0400 (7)	−0.0019 (5)	0.0023 (5)	−0.0002 (5)
O1	0.0507 (7)	0.0442 (7)	0.0502 (7)	0.0038 (5)	0.0083 (5)	−0.0071 (5)
O2	0.0372 (6)	0.0480 (7)	0.0606 (7)	−0.0060 (5)	0.0163 (5)	−0.0029 (5)
O3	0.0593 (8)	0.0293 (7)	0.0858 (9)	−0.0038 (5)	0.0090 (7)	−0.0056 (6)

C1—H1A	0.9700	C5—C6	1.408 (2)
C1—H1B	0.9700	C6—H6	0.9300
C1—C2	1.506 (2)	N1—C2	1.4523 (17)
C2—H2A	0.9700	N1—C3	1.4582 (19)
C2—H2B	0.9700	N2—H2	0.8600
C3—H3A	0.9700	N2—C4	1.445 (2)
C3—H3B	0.9700	N3—O3	1.2701 (16)
C3—C4	1.508 (2)	N3—C6	1.3406 (18)
C4—H4B	0.9700	O1—H1	0.8200
C4—H4A	0.9700	O1—C1	1.4123 (19)
C5—N1	1.3379 (17)	O2—N3	1.2702 (15)
C5—N2	1.3227 (17)
C1—O1—H1	109.5	N1—C5—C6	123.43 (13)
C1—C2—H2A	108.9	N1—C2—C1	113.42 (12)
C1—C2—H2B	108.9	N1—C2—H2A	108.9
H1A—C1—H1B	107.9	N1—C2—H2B	108.9
C2—N1—C3	121.44 (12)	N1—C3—H3A	111.0
C2—C1—H1A	109.2	N1—C3—H3B	111.0
C2—C1—H1B	109.2	N1—C3—C4	103.67 (12)
H2A—C2—H2B	107.7	N2—C5—N1	110.19 (12)
C3—C4—H4B	111.1	N2—C5—C6	126.39 (13)
C3—C4—H4A	111.1	N2—C4—C3	103.18 (12)
H3A—C3—H3B	109.0	N2—C4—H4B	111.1
C4—N2—H2	123.9	N2—C4—H4A	111.1
C4—C3—H3A	111.0	N3—C6—C5	122.59 (13)
C4—C3—H3B	111.0	N3—C6—H6	118.7
H4B—C4—H4A	109.1	O1—C1—H1A	109.2
C5—N1—C2	127.40 (12)	O1—C1—H1B	109.2
C5—N1—C3	110.75 (12)	O1—C1—C2	111.96 (12)
C5—N2—H2	123.9	O2—N3—C6	121.94 (12)
C5—N2—C4	112.19 (12)	O3—N3—O2	118.84 (12)
C5—C6—H6	118.7	O3—N3—C6	119.21 (13)
O1—C1—C2—N1	−64.63 (17)	C2—N1—C3—C4	−173.37 (14)
O2—N3—C6—C5	−0.6 (2)	C3—N1—C2—C1	−87.91 (16)
O3—N3—C6—C5	178.47 (14)	C5—N1—C2—C1	100.19 (16)
N1—C5—N2—C4	1.41 (17)	C5—N1—C3—C4	−0.24 (17)
N1—C5—C6—N3	−178.43 (12)	C5—N2—C4—C3	−1.48 (19)
N1—C3—C4—N2	0.97 (18)	C6—C5—N1—C2	−8.2 (2)
N2—C5—N1—C2	171.93 (13)	C6—C5—N1—C3	179.16 (14)
N2—C5—N1—C3	−0.69 (16)	C6—C5—N2—C4	−178.44 (14)
N2—C5—C6—N3	1.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.37	3.0463 (16)	136
N2—H2···O2	0.86	2.12	2.6600 (16)	121
O1—H1···O3ii	0.82	2.06	2.8814 (16)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.37	3.0463 (16)	136
N2—H2⋯O2	0.86	2.12	2.6600 (16)	121
O1—H1⋯O3ii	0.82	2.06	2.8814 (16)	175

Symmetry codes: (i) ; (ii) .